Addition compounds of cyclohexylamines and monocyclic phenols



Patented Feb. 6, 1940 stares rarest orr cr.

ADDITKQQN GGMKOUNDS OF CYGLDHEXYL- AIVLLNES AND MIONOCYCLKC PHENOLSGeorge L. llookenycs, Springfield, ill, assignor to Monsanto GhemicalCompany, St. Louis, Mo., a corporation of Delaware No Drawing.Application March 1, 1939, Serial No. 259,103

16 Claims.

The main objects of the invention are to pro- I vide:

Compounds-of phenol, cresol, polyphenols, or their homologues which arerelatively nonodorous; which are oil soluble; which are effective in theextermination of insect and bacterial life, and which are simple andeconomical to prepare.

These and other objects will be apparent from consideration of thefollowing description and the appendedclaims.

It has heretofore been observed that cresol and homologues thereof arehighly effective as germicidal compositions and in the eradication andprevention of such insect pests as bedbugs, cockroaches, ants and thelike. These compositions are normally applied as oil solutions ofconventional type. While highly effective for the above describedpurposes, cresol and its homologues are also characterized by a strongodor which renders them objectionable for application about the home orother places inhabited by man. Although various attempts have been madeto inhibit or mask the odor of these compounds, these efforts haveheretofore been substantially without suc cess.

The present invention is based upon the discovery that phenol,cresol,-polyphenols, and homologues and analogues thereof may be causedtoreact with primary, secondary or tertiary cyclohexylamines such ascyclohexylamine, C-aliphatic-hydrocarbon-cyclohexylamines, o alkylcyclohexylamine, o-methyl cyclohexylamine, pethyl cyclohexylamine,N-methyl amine, N-ethyl cyclohexylamine, di-cyclohexylamine,N-2-ethylhexyl cyclohexylamine, N-octyl cyclohexylamine, N -11 propylo-methylcyclohexylamine, N-benzyl cyclohexylamine, N-dimethylcyclohexyl- (Cl. MiG-563) mineral oils such as kerosene, naphtha and theusual oil vehicle employed in making up cresol solutions. These oilsolutions are substantially non-odorous and still highly toxic to"insect and bacterial life.

Cyclohexylamine may be regarded as a typical example of a compoundfalling within the above classes of amines. It reacts with cresol in theratio of two 111015 of cresol to one mol ofcyclohexylamine. However,since the reaction product practice by employing the ingredients in theratio r of 60 parts by weight of cresol to '75 by Weight ofcyclohexylamine.

An inert solvent for the reactants may be employed but it is notabsolutely necessary. In the, event it is employed, the oil vehicle (e.g., a petroleum distillate such as is used as a vehicle in fly sprays)to be employed to make up the spray functions quite satisfactorily. Theproduct requires no purification and by using the reaction medium as thespray vehicle substantial economics of materials and labor are effected.Of course, only a portion of the distillate required to make up thespray need be employed as the reaction vehicle. A concentrated solutionmay be made up and this then diluted for use. The reaction is immediateand spontaneous and is accommethods against such household pests as bed-I bugs, cockroaches and the like.

I Although substantially the full toxicity of the cresol with respect tothe insects and germicidal life is retained by the reaction product ofcresol and the cyclohexylamine, it is remarkable that I the penetratingand disagreeable odor characteristic of cresol is entirely absent.

It is to be understood that in the above described reaction,cyclohexylamine is given merely by Way of example. The cyclohexylaminevmay be replaced by any of the amines described hereinbefore and thecresol may be replaced by phenol or higher homologues including mono anddi ethyl, mono and di normal or isopropyl, butyl, isobutyl, amyl, hexyland di-isobutyl phenols. The alkyl groups in these compounds may be inortho, meta, or para positions. In addition, resorcinol, catechol,hydroquinone and pyrogallol may be used instead of cresol and thesepolyhydroxy benzenes may be substituted by hydrocarbon radicals such asthe alkyl groups mentioned above. Any of the phenolic bodies may also besubstituted by one or two chlorine or bromine atoms. However, thesolubility of the compound in oil may in some cases be reduced by thepresence of the halogen. The phenolic body is reacted with any one ofthe herein named amino bodies in accordance with the provisions of theinvention. When it is desired to accelerate the reaction, heat may beapplied. The resultant prodnets are dissolved in oil or other inertsolvents and used as insecticides and germicides in the usual manner.

These amines may be primary or secondary, that is, contain like orunlike aliphatic or cycloaliphatic groups attached to the same nitrogenatom and the aliphatic groups may be either normal or branched chains.The corresponding diamines are also contemplated.

This application is a continuation-in-part of my copending application,Serial No. 45,316, filed October 16, 1935, which has since beenabandoned.

Although only the preferred forms of the invention have been described,it is to be undertood that these are given merely by way or" example andthat numerous modifications may be made therein without departure fromthe spirit or the invention or the scope of the appended claims.

What I claim is:

1. An addition compound of a monocyclic phenol and a cyclohexylamine,said compound being soluble in oil and possessing insecticidalproperties.

2. An addition compound of a monohydroxy substituted benzene hydrocarbonand a cyclohexylamine, said compound being soluble in oil and possessinginsecticidal properties.

3. An addition compound of a monocyclic phenol and a cyclohexylaminehaving at least one hydrogen atom attached to the nitrogen atom of thecyclohexylamine, said compound being soluble in oil and possesinginsecticidal properties.

4. An addition compound of a monohydroxy substituted benzene hydrocarbonand a cyclohexylamine having at least one hydrogen atom attached to thenitrogen atom of the cyclohexylamine, said compound being soluble in oiland possessing insecticidal properties.

5. An addition compound of a monocyclic phenol and a primarycyclohexylamine, said compound being soluble in oil and possessinginsecticidal properties.

6. An addition compound of a monohydroxy substituted benzene hydrocarbonand a primary cyclohexylamine, said compound being soluble in oil andpossessing insecticidal properties.

'7. An addition compound of a monohydroxy substituted benzenehydrocarbon and cyclohexylamine, said compound being soluble in oil andpossessing insecticidal properties.

8. An addition compound of a cresol and a cyclohexylamine, said compoundbeing soluble in oil and possessing insecticidal properties.

9. An addition compound of a cresol and cyclohexylainine, said compoundbeing soluble in oil and possessing insecticidal properties.

10. A cresol-cyclohexylamine addition compound in which the componentsare combined in the ratio of two molecules of a cresol and one moleculeof cyclohexylamine, said compound being soluble in oil and possessinginsecticidal properties.

11. An addition compound of a monocyclic henol and a secondarycyclohexylamine, said compound being soluble in oil and possessing insecticidal properties.

An addition compound of a monohydroxy substituted benzene hydrocarbonand a secondary cyclohexylamine, said compound being soluble in oil andpossessing insecticidal properties.

13. An addition compound of a monohydroxy substituted benzenehydrocarbon and dicyclohexylamine, said compound being soluble in oiland possessing insecticidal properties.

14. An addition compound of a cresol and dicyclohexylamine, saidcompound being soluble in oil and possessing insecticidal properties.

15. An addition compound of a monocyclic phenol and a C-alkylcyclohexylamine, said compound being soluble in oil and possessinginsecticidal properties.

16. An addition compound of a cresol and C- ortho-methylcyclohexylamine, said compound being soluble in oil and possessinginsecticidal properties.

GEORGE L. HOCKENYOS.

